In his works, Rolle provides little explicit evidence about his early life and education. Most, if not all, of our information about him comes from the Office of Lessons and Antiphons that was composed in the 1380s in preparation for his canonisation, although this never came about.
Born into a small farming family and brought up at Thornton-le-Dale near Pickering, he studied at the University of Oxford, where he was sponsored by Thomas de Neville, the Archdeacon of Durham. While there, he is said to have been more interested in theology and biblical studies than philosophy and secular studies. He left Oxford at age eighteen or nineteen – dropping out before he received his MA – to become a hermit. Leaving the family home, he first went to Pickering, and housed with a squire, John Dalton, for perhaps three years.
It was probably while still living with Dalton, two years and eight months after becoming a hermit, Rolle had his first mystical experience. Around a year later, he felt similarly after listening to a choir, and he began to take less interest in all things temporal.
Dalton himself was arrested and his lands confiscated in 1322; the lack of mention of this fact in accounts of Rolle's life makes it likely that he was no longer living with Dalton by this point.
"I felt within me a merry and unknown heat...I was expert it was not from a creature but from my Maker, as it grew hotter and more glad."
—Rolle on his first mystical experience.
It is unclear where Rolle lived from 1321/2 until his death in 1349. One theory is that Rolle spent the early 1320s at the renowned Sorbonne, becoming well-trained in theology, and perhaps being ordained there. This theory is based on the entries in three seventeenth-century manuscripts at the Sorbonne, assumed to be copies of medieval originals, which record a Ricardus de Hampole as being admitted to the Sorbonne in 1320, entering the prior's register in 1326, and noting that he died in 1349 among the sisters of Hampole near Doncaster in Yorkshire. Scholars, however, are divided on the authenticity of this material. Whether or not Rolle studied in Paris, it is probable that most if not all of this time was spent in Richmondshire, either living with his family at Yafforth, or, given the uncertain political conditions in the region at the time, wandering from patron to patron.
Around 1348, Rolle knew the Yorkshire anchoress Margaret Kirkby, who was his principal disciple and the recipient of much of his writings and would be important in establishing his later reputation.
Rolle died in Michaelmas 1349 at the Cistercian nunnery at Hampole. Because of his time spent here, where he was director of the inmates, he is sometimes known as Richard Rolle of Hampole, or de Hampole. It is unclear what his function was there: he was not the nuns' official confessor, who was a Franciscan (in any case, it is unlikely he would have had ecclesiastical sanction for this, since unless the theory about his ordination in Paris is correct, he was probably not ordained, since his name is not in the list of those ordained in the dioceses of York or Durham in the relevant years). However he wrote The Form of Living and his English Psalter for a nun there, Margaret Kirkby (who later took up a similar life to Rolle, as an anchoress), and Ego Dormio for a nun at Yedingham. It is possible that he died of the Black Death, but there is no direct evidence for this. He was buried first in the nuns' cemetery at Hampole. Later records of people making offerings of candles at his shrine show that he was moved first to the chancel and then to his own chapel.